N-phenyl-2-hydroxymethyl-5-hydroxy-γ-pyridone | 70033-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-phenyl-2-hydroxymethyl-5-hydroxy-γ-pyridone
• 英文别名: 3-hydroxy-6-hydroxymethyl-1-phenyl-4-pyridinone；5-hydroxy-2-hydroxymethyl-1-phenylpyridin-4-one；5-hydroxy-2-hydroxymethyl-1-phenyl-4-pyridone；5-hydroxy-2-hydroxymethyl-1-phenyl-1H-pyridin-4-one；5-Hydroxy-2-hydroxymethyl-1-phenyl-pyridin-4-one；5-Hydroxy-2-(hydroxymethyl)-1-phenylpyridin-4(1H)-one；5-hydroxy-2-(hydroxymethyl)-1-phenylpyridin-4-one
• CAS: 70033-61-3
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: JFSCKVXXRWUABD-UHFFFAOYSA-N

物化性质

• 熔点：
  238 °C(Solv: methanol (67-56-1))
• 沸点：
  403.8±45.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  密封保存，在干燥处，2-8°C

反应信息

• 作为反应物：
  描述：

  N-phenyl-2-hydroxymethyl-5-hydroxy-γ-pyridone 在 氯化亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-((benzo[d]thiazol-2-ylthio)methyl)-5-hydroxy-1-phenylpyridin-4(1H)-one
  参考文献：
  名称：

  优化Ø 3酰基曲酸衍生物的强效选择性人中性粒细胞弹性蛋白酶抑制剂

  摘要：

  人嗜中性粒细胞弹性蛋白酶（HNE）是治疗慢性和急性炎症性肺疾病的有吸引力的靶标。报道了曲酸支架的优化运动以开发新的有效HNE抑制剂。O 3-新戊酰基衍生物是最有效的抑制剂，IC 50值低至80 nM。这些化合物具有出色的选择性和细胞毒性，并具有合适的配体效率。

  DOI：

  10.1021/jm4011725
• 作为产物：
  描述：

  曲酸 、 苯胺 在 盐酸 作用下， 以 水 为溶剂， 生成 N-phenyl-2-hydroxymethyl-5-hydroxy-γ-pyridone
  参考文献：
  名称：

  优化Ø 3酰基曲酸衍生物的强效选择性人中性粒细胞弹性蛋白酶抑制剂

  摘要：

  人嗜中性粒细胞弹性蛋白酶（HNE）是治疗慢性和急性炎症性肺疾病的有吸引力的靶标。报道了曲酸支架的优化运动以开发新的有效HNE抑制剂。O 3-新戊酰基衍生物是最有效的抑制剂，IC 50值低至80 nM。这些化合物具有出色的选择性和细胞毒性，并具有合适的配体效率。

  DOI：

  10.1021/jm4011725

文献信息

• Synthesis, characterization, and biological relevance of hydroxypyrone and hydroxypyridinone complexes of molybdenum
  作者：Sarah J Lord、Noah A Epstein、Robert L Paddock、Christopher M Vogels、Tracy L Hennigar、Michael J Zaworotko、Nicholas J Taylor、William R Driedzic、Tom L Broderick、Stephen A Westcott

  DOI：10.1139/v99-111

  日期：1999.7.1

  We have prepared a number of complexes of the type cis-MoO₂L₂ where L represents a hydroxypyronato or hydroxypyridinonato ligand. Both the maltol (3-hydroxy-2-methyl-4-pyrone, Hma) and kojic acid (5-hydroxy-2-hydroxymethyl-4-pyrone, Hka) complexes, cis-MoO₂(ma)₂ (1) and cis-MoO₂(ka)₂ (2), have been characterized by X-ray diffraction studies. The pyrone ligands are bound to molybdenum in a cis bidentate fashion via the deprotonated hydroxyl groups and the ketone moieties. Crystals of 1 are orthorhombic, a = 12.107 (1), b = 8.6169 (8), c = 16.472 (1) Å, Z = 4, space group Pca2₁, and those of 2 are monoclinic, a = 8.4591 (5), b = 16.3453 (10), c = 10.2954 (7) Å, β = 103.0320 (10)°, Z = 4, space group P2₁/c. Hydroxypyridinone molybdenum complexes have been prepared for both maltol and kojic acid derivatives with the substituents Me, n-Pr, CH₂Ph, Ph at the ring nitrogen. Crystals of the 3-hydroxy-2-methyl-1-phenyl-4-pyridinone (Hppp) derivative, MoO₂(ppp)₂ (9), are monoclinic, a = 10.9476 (6), b = 13.5353 (9), c = 17.4877 (10) Å, β = 93.465 (4)°, Z = 4, space group P2₁/n. Initial investigations into the effects molybdenum compounds have on diabetic hearts are presented. Both Na₂MoO₄ (used as a control) and 1 were effective in lowering blood glucose and free fatty acid levels. Diabetic rats treated with molybdate showed significant improvements in postischemic cardiac function.Key words: molybdenum, hydroxypyrones, hydroxypyridinones, heart function.

  我们已经准备了一系列cis-MoO₂L₂类型的配合物，其中L代表羟基吡啶酮或羟基吡啶酮配体。麦芽酮（3-羟基-2-甲基-4-吡喃酮，Hma）和曲酸（5-羟基-2-羟甲基-4-吡喃酮，Hka）配合物，cis-MoO₂(ma)₂（1）和cis-MoO₂(ka)₂（2），已经通过X射线衍射研究进行了表征。吡喃酮配体以顺式双齿方式通过去质子羟基和酮基与钼结合。1的晶体为正交晶系，a = 12.107（1），b = 8.6169（8），c = 16.472（1）埃，Z = 4，空间群Pca2₁，而2的晶体为单斜晶系，a = 8.4591（5），b = 16.3453（10），c = 10.2954（7）埃，β = 103.0320（10）°，Z = 4，空间群P2₁/c。已经为麦芽酮和曲酸衍生物制备了羟基吡啶酮钼配合物，其在环氮原子处具有Me、n-Pr、CH₂Ph、Ph等取代基。3-羟基-2-甲基-1-苯基-4-吡啶酮（Hppp）衍生物MoO₂(ppp)₂（9）的晶体为单斜晶系，a = 10.9476（6），b = 13.5353（9），c = 17.4877（10）埃，β = 93.465（4）°，Z = 4，空间群P2₁/n。首次研究了钼化合物对糖尿病心脏的影响。钼酸钠（用作对照）和1在降低血糖和游离脂肪酸水平方面均有效。接受钼酸盐治疗的糖尿病大鼠在缺血后心脏功能方面表现出显著改善。关键词：钼、羟基吡喃酮、羟基吡啶酮、心脏功能。
• SMALL MOLECULE INSULIN MIMETICS ABSENT QUINONES
  申请人：Pirrung C. Michael

  公开号：US20070232663A1

  公开（公告）日：2007-10-04

  Compounds of Formula I are described along with pharmaceutical formulations thereof, and methods of treating disorders such as diabetes and neurodegenerative diseases with such compounds.

  公式I的化合物以及其药物配方被描述，以及使用这些化合物治疗糖尿病和神经退行性疾病的方法。
• Substituent Effects on the Dissociation Constants of 1-Aryl-5-hydroxy-2-hydroxymethyl-4-pyridones
  作者：Kimiaki Imafuku、Kumio Takahashi、Hisashi Matsumura

  DOI：10.1246/bcsj.56.1879

  日期：1983.6

  Six new 1-aryl-5-hydroxy-2-hydroxymethyl-4-pyridones were synthesized and their dissociation constants were measured. Hammett analysis of pKa values for proton gain and proton loss gave the following equations: pK1=2.74–0.34σ and pK2=8.80–0.36σ, respectively.

  合成了六个新的 1-芳基-5-羟基-2-羟甲基-4-吡啶酮并测量了它们的解离常数。质子增益和质子损失的 pKa 值的哈米特分析给出了以下等式：分别为 pK1=2.74–0.34σ 和 pK2=8.80–0.36σ。
• Small molecule insulin mimetics absent quinones
  申请人：Duke University

  公开号：US08222279B2

  公开（公告）日：2012-07-17

  Compounds of Formula I are described along with pharmaceutical formulations thereof, and methods of treating disorders such as diabetes and neurodegenerative diseases with such compounds.

  本文描述了I式化合物及其制药配方，并介绍了使用这些化合物治疗糖尿病和神经退行性疾病的方法。
• INHIBITORS OF CATECHOL O-METHYL TRANSFERASE AND THEIR USE IN THE TREATMENT OF PSYCHOTIC DISORDERS
  申请人：Wolkenberg Scott

  公开号：US20130084346A1

  公开（公告）日：2013-04-04

  The present invention relates to 4-pyridinone compounds which are inhibitors of catechol O-methyltransferase (COMT), and are useful in the treatment and prevention of neurological and psychiatric disorders and diseases in which COMT enzyme is involved. The present invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which COMT is involved.

  本发明涉及4-吡啶酮类化合物，它们是儿茶酚-O-甲基转移酶(COMT)的抑制剂，适用于治疗和预防神经和精神障碍以及COMT酶参与的疾病。本发明还涉及包含这些化合物的药物组合物以及这些化合物和组合物在预防或治疗COMT参与的这类疾病中的使用。